GB1439682A - Bromination of n-containing heterocycles - Google Patents
Bromination of n-containing heterocyclesInfo
- Publication number
- GB1439682A GB1439682A GB5046973A GB5046973A GB1439682A GB 1439682 A GB1439682 A GB 1439682A GB 5046973 A GB5046973 A GB 5046973A GB 5046973 A GB5046973 A GB 5046973A GB 1439682 A GB1439682 A GB 1439682A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromination
- phenylpyrimidine
- naphthyridine
- maintaining
- containing heterocycles
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000623 heterocyclic group Chemical group 0.000 title abstract 3
- 230000031709 bromination Effects 0.000 title abstract 2
- 238000005893 bromination reaction Methods 0.000 title abstract 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 abstract 1
- CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 abstract 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 abstract 1
- XGNQDLUHEFXGPL-UHFFFAOYSA-N 3,8-dibromo-1,6-naphthyridine Chemical compound BrC1=CN=CC2=CC(Br)=CN=C21 XGNQDLUHEFXGPL-UHFFFAOYSA-N 0.000 abstract 1
- ZGIKWINFUGEQEO-UHFFFAOYSA-N 3-bromoquinoline Chemical compound C1=CC=CC2=CC(Br)=CN=C21 ZGIKWINFUGEQEO-UHFFFAOYSA-N 0.000 abstract 1
- SCRBSGZBTHKAHU-UHFFFAOYSA-N 4-bromoisoquinoline Chemical compound C1=CC=C2C(Br)=CN=CC2=C1 SCRBSGZBTHKAHU-UHFFFAOYSA-N 0.000 abstract 1
- MKLQPIYLZMLAER-UHFFFAOYSA-N 4-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=CC=NC=N1 MKLQPIYLZMLAER-UHFFFAOYSA-N 0.000 abstract 1
- SDPYFZLDWYNXJF-UHFFFAOYSA-N 5-bromo-4-phenylpyrimidine Chemical compound BrC1=CN=CN=C1C1=CC=CC=C1 SDPYFZLDWYNXJF-UHFFFAOYSA-N 0.000 abstract 1
- GYCPLYCTMDTEPU-UHFFFAOYSA-N 5-bromopyrimidine Chemical compound BrC1=CN=CN=C1 GYCPLYCTMDTEPU-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- -1 halide salt Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1439682 Bromination of N-containing heterocycles ELI LILLY & CO 30 Oct 1973 [21 Nov 1972] 50469/73 Heading C2C Pyrimidine, quinoline, isoquinoline, 4- phenylpyrimidine and 1,6-naphthyridine are brominated by co-mingling the heterocyclic compound as its H. halide salt with a solvent substantially inert to the action of Br 2 under the reaction conditions, heating and maintaining the mixture at 125-200 C., adding Br 2 to the mixture over a period of 30-90 minutes, and maintaining at 125-200 C. for a further 2-6 hours. The preferred solvents are nitrobenzene, o-dichlorobenzene, o-nitroanisole, o-nitrotoluene and benzonitrile. The heterocyclic salt used is advantageously the hydrochloride. Amongst the examples 5-bromopyrimidine, 3 - bromoquinoline, 4 - bromoisoquinoline, 5 - bromo - 4 - phenylpyrimidine and 3,8 - dibromo - 1,6 - naphthyridine are prepared.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30838972A | 1972-11-21 | 1972-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1439682A true GB1439682A (en) | 1976-06-16 |
Family
ID=23193800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5046973A Expired GB1439682A (en) | 1972-11-21 | 1973-10-30 | Bromination of n-containing heterocycles |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS596854B2 (en) |
| BE (1) | BE807525A (en) |
| CH (1) | CH584205A5 (en) |
| DE (1) | DE2356358C2 (en) |
| FR (1) | FR2207100B1 (en) |
| GB (1) | GB1439682A (en) |
| IL (1) | IL43505A (en) |
| IT (1) | IT1001824B (en) |
| NL (1) | NL184058C (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2221808C2 (en) * | 1972-05-04 | 1985-06-20 | Sandoz-Patent-GmbH, 7850 Lörrach | Hydrazinopyridazine derivatives, their acid addition salts, processes for their preparation and medicines |
-
1973
- 1973-10-29 IL IL43505A patent/IL43505A/en unknown
- 1973-10-30 GB GB5046973A patent/GB1439682A/en not_active Expired
- 1973-11-06 CH CH1558773A patent/CH584205A5/xx not_active IP Right Cessation
- 1973-11-12 DE DE2356358A patent/DE2356358C2/en not_active Expired
- 1973-11-16 IT IT31462/73A patent/IT1001824B/en active
- 1973-11-16 NL NLAANVRAGE7315788,A patent/NL184058C/en not_active IP Right Cessation
- 1973-11-20 BE BE1005515A patent/BE807525A/en not_active IP Right Cessation
- 1973-11-21 FR FR7341410A patent/FR2207100B1/fr not_active Expired
- 1973-11-21 JP JP48131177A patent/JPS596854B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL184058B (en) | 1988-11-01 |
| FR2207100A1 (en) | 1974-06-14 |
| IT1001824B (en) | 1976-04-30 |
| DE2356358A1 (en) | 1974-05-30 |
| BE807525A (en) | 1974-05-20 |
| IL43505A0 (en) | 1974-01-14 |
| NL184058C (en) | 1989-04-03 |
| JPS596854B2 (en) | 1984-02-15 |
| FR2207100B1 (en) | 1981-06-19 |
| DE2356358C2 (en) | 1984-12-06 |
| NL7315788A (en) | 1974-05-24 |
| JPS4981375A (en) | 1974-08-06 |
| CH584205A5 (en) | 1977-01-31 |
| IL43505A (en) | 1977-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19931029 |